(E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enyl methyl carbonate

Base Information

• Chemical Name: (E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enyl methyl carbonate
• CAS No.: 939017-97-7
• Molecular Formula: C₂₅H₄₄O₅Si₂
• Molecular Weight: 480.792
• Mol file: 939017-97-7.mol

Synonyms:(E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enyl methyl carbonate

Chemical Property of (E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enyl methyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enyl methyl carbonate

There total 7 articles about (E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enyl methyl carbonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

(E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-en-1-ol (939017-96-6) + methyl chloroformate (79-22-1) → (E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enyl methyl carbonate (939017-97-7)

Guidance literature:

With pyridine; In dichloromethane; at 5 - 20 ℃; for 0.5h;

DOI:10.1021/jo062447h

Reference yield:

2-allyl-1,3-bis(methoxymethoxy)benzene (939017-92-2) → (E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enyl methyl carbonate (939017-97-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2.97 g / aq. HCl / tetrahydrofuran; methanol / 36 h / Heating

2.1: 79 percent / imidazole / acetonitrile / 18 h / 20 °C

3.1: ozone / CH₂Cl₂ / -80 - -70 °C

3.2: 89 percent / acetic acid; zinc / CH₂Cl₂ / 0 °C

4.1: 86 percent / LiCl; DBU / acetonitrile / 18 h / 20 °C

5.1: 77 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

6.1: 82 percent / pyridine / CH₂Cl₂ / 0.5 h / 5 - 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 4.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo062447h

Reference yield:

ethyl (E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enoate (939017-95-5) → (E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-enyl methyl carbonate (939017-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

2: 82 percent / pyridine / CH₂Cl₂ / 0.5 h / 5 - 20 °C

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo062447h

upstream raw materials:

(E)-4-(2,6-bis(tert-butyldimethylsilyloxy)phenyl)-2-methylbut-2-en-1-ol

methyl chloroformate

2-allyl-1,3-bis(methoxymethoxy)benzene

2-allyl-1,3-bis(tert-butyldimethylsilyloxy)benzene

Downstream raw materials:

(E)-4-(2,6-dihydroxyphenyl)-2-methylbut-2-enyl methyl carbonate